Acetic Acid → N-Isopropyl-3-broMoaniline

Temperature

0 °C

Sodium borohydride (16.5 g, 435 mmol) was added slowly over 2 hours to a mixture of 3-bromoaniline (10 g, 58.13 mmol), ethanol (58 mL), acetic acid (50 mL, 866.1 mmol), water (140 mL), acetone (35 mL, 482.5 mmol), and sodium acetate (15.8 g, 116.2 mmol). The solution was stirred at 0° C. for 3 hours. The reaction mixture was poured into 1:1 mixture of ether and hexane containing 2N KOH. The layers were separated and the aqueous layer was extracted with ether/hexane (1:1). The combined organic layers were washed once with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.31) to give the title compound (23.10 g, 93% as an oil:

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with ether/hexane (1:1)
3. washThe combined organic layers were washed once with water and brine
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.31)

ORD record

ord-69262a77297e40e0ad93be9708005277

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127382